Trifluoroacetic acid → HCID 178429616, compound

HRID 2412468Notes

Reaction equation

HRID 2412468 reaction equation
[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:16]([NH:17][C:18]3[NH:19][CH:20]=[C:21]([CH2:23][CH2:24][NH:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[N:22]=3)[C:15](=[O:32])[N:6]2[C:7]=1[C:8]([O:10]C(C)(C)C)=[O:9].[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:16]([NH:17][C:18]3[NH:19][CH:20]=[C:21]([CH2:23][CH2:24][NH:25][C:26](=[O:31])[C:27]([F:28])([F:30])[F:29])[N:22]=3)[C:15](=[O:32])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178429604HCID 178429604, compound

Product 1

HCID 178429616HCID 178429616, compound

Procedure

A suspension of t-butyl 3-methyl-7-[4-(2-trifluoroacetylaminoethyl)imidazol-2-yl]aminoceph-3-em-4-carboxylate (0.34 g.) in TFA (5 ml.) was stirred for 2 hours at ambient temperature and then evaporated to dryness. The residue was purified by precipitation from a THF solution with ether to give 3-methyl-7-[4-(2-trifluoroacetylaminoethyl)imidazol-2-yl]aminoceph-3-em-4-carboxylic acid trifluoroacetate as a cream solid (0.2 g.), m.p. 165° (decomp.), having the following n.m.r. spectrum in CH3OD: 2.14 (s, 3H); 2.82 (t, 2H); 3.5 (m, 4H); 5.14 (d, 1H); 5.38 (d, 1H); 6.7 (s, 1H).

Workup

  1. customevaporated to dryness
  2. customThe residue was purified by precipitation from a THF solution with ether

Sources & evidence

ORD record
ord-35616e7bd9384905b8a6b97b88754b1d
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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